Shelbyville Rentals USA Kentucky Louisville Shelbyville

Upscale Kentucky Bourbon Trail & Close to Louisville | House in Shelbyville

9.8 (9 Reviews) |   2 Bedrooms  2 Bathrooms  4 Guests  Stay&Play
Shelbyville House | Upscale Kentucky Bourbon Trail & Close to Louisville

2 Bedroom House in Shelbyville

Welcome to The Oak, an upscale first floor 2-bedroom, 2-bath retreat in the heart of Kentucky's Bourbon Trail. Located in historic downtown Shelbyville, this 1909 house has been painstakingly restored to highlight its charm. Enjoy tasteful décor (including local artwork by the 148th Kentucky Derby artist), plush furnishings, and a fully-equipped kitchen. Relax on the patio or enjoy boardgames after a day at the famous bourbon distilleries and horse farms. Walk to dinner and shops. Retreat to elegant bedrooms with premium linens. The Oak offers the perfect base for bourbon and horse enthusiasts. Book now for a memorable experience of luxury and comfort.
The Oak is located at 1029 Main Street. Experience the smalltown charm of historic Shelbyville Kentucky, where you can walk to local boutique shops and restaurants. Shelbyville is the Saddlebred Capital of the World and boasts a central location between Louisville, Lexington and Bardstown in the heart of the Kentucky Bourbon Trail. Connect with locals, embrace the culture, and create memorable moments at The Oak in Shelbyville, KY.
The Property
We offer 2 queen bedrooms and 2 full bathrooms with tiled showers, 1 of which is ensuite.
We offer a living space complete with a living room, a smart TV and a fully stocked kitchen.
We also offer a covered patio and grill for your evening BBQ. (It is shared with our connected property the Copper)
Kitchen-The fully stocked kitchen is ready for guests to eat, drink and be merry. Each has an attached dining space for 4
Coffee- A Keurig Coffee machine is provided along with enough pods, sweeteners, and creamer to get you started.
Enjoy cards and boards games with friends and family for added enjoyment
Two private off street parking spaces are available at the rear of the property.
Guest access
Guests will have full access to the property other than the garage area. Please note that the Oak is a 1st Story Unit.
Other Items of interest
Signature cocktail welcome kit included featuring local bitters and mixer (BYOB- Bring your own Bourbon)
Bathroom toiletries provided (shampoo, conditioner, body wash, lotion, bar soap)
Contactless check in and check out through our smart lock system
If your visit includes the bourbon trail, please make your tour reservations well in advance as spaces fill up fast.
Within a 50 mile radius of The Oak you'll find dozens of the most famous bourbon distilleries offering unique flavors and experiences (and you'll enjoy Kentucky's scenic countryside and horse farms along the way).
Bulleit Distilling Co. (4 mi)
Jeptha Creed Distillery (4.8 mi)
Whiskey Thief Distilling Co. (14 mi)
Heaven's Door Distillery (coming Sept. 2023) (14 mi)
Kentucky Artisan Distillery (20 mi)
Buffalo Trace Distillery (23 mi.)
Wild Turkey Distillery (26 mi)
Castle & Key Distillery (28 mi)
Four Roses Distillery (29 mi)
Woodford Reserve Distillery (30 mi)
Rabbit Hole Distillery (30 mi)
Angel's Envy Distillery (31 mi)
Old Forester Distilling Co. (32 mi)
Michter's Fort Nelson Distillery (32 mi)
Evan Williams Experience (32 mi)
Peerless Distillery (32 mi)
Copper & Kings (34 mi)
Stitzel-Weller Distillery (37 mi)
Bardstown Bourbon Co. (40 mi)
Lux Row Distillers (41 mi)
Heaven Hill Distillery (42 mi)
Willett Distillery (43 mi)
RD1 Spirits (44 mi)
Preservation Distillery (44 mi)
Jim Beam Distilling Co. (46 mi)
Other Kentucky experiences you won't want to miss:
Shelby Co. Fairgrounds and Horse Show (0.8 mi)
Valhalla Golf Course (14 mi)
Kentucky's historic Capitol (20 mi)
Churchill Downs & Kentucky Derby Museum (31 mi)
Belle of Louisville Riverboat (31 mi)
Louisville Slugger Museum (32 mi)
Keeneland Racetrack (40 mi)
Kentucky Horse Park (46 mi)
No candles are allowed to be burned in the home.
No one other than guests within the reservation are permitted to stay at the home.
To Ensure a smooth stay, guests will be required to review and sign our rental agreement upon booking confirmation.

Upscale Kentucky Bourbon Trail & Close to Louisville is located in Shelbyville. Upscale Kentucky Bourbon Trail & Close to Louisville provides accommodation, featuring Parking, Sports/Activities, Wellness Facilities, among other amenities. This House features Parking, Sports/Activities, Wellness Facilities, to make your stay a comfortable one.

Upscale Kentucky Bourbon Trail & Close to Louisville has 2 Bedrooms , 2 Bathrooms, and max occupancy of 4 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Shelbyville has interesting places to visit. If you want to learn more about the House in Shelbyville, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • TV
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Wellness Facilities
  • Fireplace/Heating
  • Guest Services
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Pets not allowed
Smoking Policy Smoking is not permitted
Other Policy Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher and a first aid kit special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation
 
Shelbyville, 40065, United States

What Our Guests say 500 + Reviews

Mar 27, 2025 03:41:00 AM
Summary: We stayed three nights and toured several distilleries in the area such as angel’s envy and buffalo trace. Our accommodations were exceptional. The home was well stocked, spacious enough for the four of us and the furnishings were comfortable and modern. The hosts were readily available for any issues or questions. Excellent place to stay!
Ollie W. Ollie W.
Dec 17, 2024 09:17:53 PM
Summary: Everything about our getaway was perfect. We arrived to the house around 9 and the keyless entry was flawless. The house was exactly as the pictures described and was perfect for two couples. The decor of the home was nicely created and felt very homey. We spent most of our time on the Bourbon Trail and loved the location so we could get to where we were going in about 30 to 45 minutes. Buffalo Trace was a daily stop and was a 30 minute drive. We’d definitely recommend this home.
Beth G. Beth G.
Aug 29, 2024 06:33:57 AM
Summary: If you are looking for a place to stay while checking out the Bourbon Trail, this is an ideal location. Quiet and very clean. Easy access to the different regions of the Bourbon Trail. We highly recommend.
Sharla W. Sharla W.
Jun 9, 2024 12:56:56 AM
Summary: What a beautiful property. Love the dark makeup towels provided and the mixed drink suggestion. The convenience was great. In between Louisville and Lexington. Nice small town to explore. Would definitely go again. Thanks for experience.
May 31, 2024 02:45:07 AM
Summary: The Oak is on the bottom floor of a 2 story STR. It was very clean, with a spacious and well-stocked kitchen and dining area. The living room was cozy as were the 2 bedrooms. This is a very old building and we could hear the people above us enjoying themselves when we were in the living room. This property is an easy walk to downtown and restaurants. It is also right next door to a pizza shop and convenience store. We did need to contact management over a few, small issues that were very quickly addressed and corrected.
mary anne a. mary anne a.
Sep 22, 2023 08:21:38 PM
Summary: Loved this stay - We took a trip to celebrate a couple of 30th birthday's on the Bourbon Tour and this was the perfect house for it. Very great location to the distilleries, restaurants, and coffee shops. The place was very clean and beautifully updated. The managers stayed in contact with us during our stay, but we never needed anything as it was ready for us when we arrived!
Kelcey S. Kelcey S.
Aug 11, 2023 11:32:20 PM
Summary: Very convenient location in Shelbyville-- easy drive into Louisville and Frankfort.
Doris T. Doris T.
Jul 12, 2023 01:48:14 AM
Summary: This property was a great homebase for our stops on the Bourbon Trail. Nicely remodeled and well appointed with all the basics. Neighborhood can be occasionally loud as the fire station is a block away.
Danielle H. Danielle H.

FAQ's

Is this Shelbyville house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Shelbyville house have a swimming pool?

No, this Shelbyville house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Shelbyville house?

Best-rates for the Shelbyville house starts from $285 per night with includes Parking, Sports/Activities, Wellness Facilities, Barbecue/Outdoor Cooking, Balcony/Terrace, Security/Safety, Fireplace/Heating, Guest Services, Entertainment, Kitchen, Child Friendly, Internet, Air Conditioner, TV, Laundry StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Shelbyville house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Shelbyville house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Shelbyville house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Shelbyville house?

Based on the information reported by the owner or manager, the Shelbyville house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Shelbyville house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Shelbyville house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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